


How to Pick Up a Wallflower: A Guidebook

by eiter



Category: Supernatural
Genre: Alternate Universe - High School, Bi!Dean, Destiel - Freeform, F/F, Fluff, Friends to Lovers, M/M, Romance, UST, also a bit of bullying but nothing serious, john is being his usual abusive self so be warned, nerd!cas, the main characters are of age
Language: English
Status: In-Progress
Published: 2016-12-01
Updated: 2016-12-03
Packaged: 2018-09-03 11:01:42
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,050
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8709907
Author URL: https://archiveofourown.org/users/eiter/pseuds/eiter
Summary: Dean is in love with his best friend, but Cas is a clueless wallflower.





	1. Chapter 1

**Author's Note:**

> Warning: unbeta'd.
> 
> You can read this fic in Russian [here](https://ficbook.net/readfic/4925843).

“Hey, Cas!”

Dean leans against the lockers with a wide grin on his face. Cas flinches in surprise and drops the stack of books he was holding in his hands. Dean hurries to help him pick them up only to bump their foreheads together.

“Hello, Dean.”

Cas stands up, clutching the books tightly to his chest and adjusting the glasses that slipped down his nose with his free hand.

“You know, sometimes I can't believe they let you be a team captain.”

Dean can feel his cheeks burning. Embarrassed, he hands over the comic book that fell out of one of the schoolbooks. Cas gives him an encouraging smile and squints short-sightedly as he looks up at the clock on the wall.

“My class is about to start. See you later.”

“How about lunch?”

“Only if you promise not to stab me with a fork.”

Dean is still grinning after Cas when Charlie walks up behind him.

“That's not exactly what I meant by 'you need a strategy'. Are you sure he's gonna fall in love with you if you beat him up a few times? ‘Cause I don’t think that’s how it works.”

Dean throws his head back with a groan, and Charlie jokingly pats him on the shoulder.

“You're hopeless, Winchester.”

“Shut up, Bradbury.”

  


She comes around later that day, and they spend the evening together. Charlie and Sam are too busy with their gamer battle to pay attention to the now almost cold pizza, so Dean seizes the opportunity.

“Dad's away on a business trip again,” Dean shares with his mouth full, eyes glued to the comic book he borrowed from Cas.

“Sleepover!” immediately reacts Charlie. “Nobody's going anywhere until I win.”

“I think you just mispronounced my name,” corrects her Sammy, staring at the screen with a manic look on his face. Dean eyes him skeptically and shakes his head in disapproval.

“It's time for someone to go to bed.”

“But I'm killing it!” Sam knows that whining will get him nowhere so he moves on to bargaining. “Let me stay up for a little bit longer, and I'll write that essay for you.”

“…damn, you got me.” Dean raises his hands as a sign of defeat. Charlie clicks her tongue, clearly not being the biggest fan of child labor. Dean tries to justify himself.

“What? I can't keep copying off Cas till the end of high school.”

Without saying a word, Charlie reaches into her pocket, pulls out a crumpled five-dollar bill and hands it over to smug-looking Sam. Waiting for an explanation, Dean clears his throat to get their attention.

“We made a bet about how long you can go without mentioning your boyfriend,” Charlie teases him. “You owe me five bucks, Winchester.”

“He is not my boyfriend,” grumbles Dean, hiding his face behind the page he is reading. “And stop corrupting my little brother with money bets.”

“Dean, you pay me for cleaning up around the house. And for doing your homework.”

Completely satisfied with himself, Sam gets a slight whack on the head. They laugh it off and finish what’s left of their pizza. Sammy wins in the game, and even though Dean suspects Charlie was not trying her hardest he is grateful for the broad smile on Sam’s face.

Sam goes to bed, and they relocate into the kitchen to help themselves with some of John Winchester’s beer stock.

“Have you ever noticed how the Novaks are too… faithful even for a province like ours?” Charlie carefully chooses her words.

“The last time I’ve been to Chuck’s sermon, he called himself God,” chuckles Dean. “Dad never made neither me or Sammy go to church ever since.”

“If Anna’s parents find out about us, we’ll have to skip town. Or country,” sourly muses Charlie.

“That bad, huh?”

“Anna’s missed one of her Sunday morning services because of our date and was grounded for a month. Not that it stopped me from coming over through the window…”

She notices she got Dean upset and thinking about something else and bites her lip.

“And what does Cas think about it?” Dean makes an effort to look indifferent but fails miserably.

“Well, you know Cas. The guy’s clueless. I doubt he’d realize we were together even if we kissed right in front of him. ‘Sides, he knows you play for both teams, and you’re still best friends.”

Dean takes a swig of his beer to help himself swallow the lump in his throat left by the F word. It’s way past midnight, his head is growing heavy from the beer, and they both have classes in the morning.

“Why can’t you just tell him everything? ‘Hey, Cas, I’ve been into you for the past few years, and you’re probably the last person in school who doesn’t know it yet. Please kiss me before I drive poor Charlie completely nuts’… Oh wait, I forgot. Dean Winchester would sooner die than talk about his feelings.”

“My pining is nothing compared to what I’ve heard about your love life.”

Dean winks, and Charlie blushes.

“I’m never playing Truth or Dare with you again.”

  


Dean misses yet another football practice for a couple of hours in the library with Cas who doesn’t give up easily on helping him with the subjects he’s successfully failing. Apparently, it’s even harder to concentrate on studying when the most attractive guy he’s ever met is sitting across the table. Looking at him through the thick lenses of his glasses that make his eyes seem disproportionally huge, wearing old wool sweater that’s too big for him and running his fingers through his unruly hair. Dean is honestly doing his best to keep the train of thought but the quiet soft voice gets in the way, and all that he’s learnt in the past hour is how smooth and tanned Cas’ skin is.

“Dean, are you listening?”

Cas looks up from his notes and Dean catches a glint of disappointment in his eyes. He hastily nods and scribbles something unintelligible in his notebook.

“Yep, yeah, probably… probability… theory…”

“We don’t have to sit here all day.” His face lights up with a warm smile and Dean relaxes. “We can go for a pie before the bakery is closed and you’re bored to death.”

“I don’t wanna seem like an ungrateful a-hole because I am really grateful… But who in their right mind would refuse a piece of good pie?”

Dean enthusiastically sweeps his notes into the bag and helps Cas with his trench coat. The librarian gives them the eye and hushes them but Dean is already pulling Cas towards the exit.

Today is Tuesday, and Tuesday can only mean one thing: blueberry pie. They sit at their usual table, and while Dean is biting down on his hot sweet piece of the most delicious pie in history, Cas takes a heavy schoolbook out of his bag and disappears behind its cover with a cup of steamy coffee in his hand.

Dean feels guilty for wasting his friend’s time. After all, he does not have to help him just because instead of preparing for the exams Dean is busy with football practices and matches and Cas was just lucky enough to be a nerd. Dean may be shameless but he cannot exploit his friend’s kindness at his expense. Especially considering how slowly he is making progress.

“Look, Cas, I should’ve said this sooner,” Dean takes a deep breath and blurts out, “I’ve never thanked you for helping me with school so, huh, thanks, I guess. I know you gotta get ready for the exams, too, and I’m just wasting your time. I mean, damn, you don’t even have the time to eat properly-”

“Dean,” gently interrupts him Cas, peeking from behind the book. “I always have time for you.”

Dean can feel the tips of his ears burning and opens his mouth to try and prove his point when Cas adds, grinning, “Besides, unlike some of us, I know how to properly schedule my time. And there’s a comic book hidden in my copy of trigonometry, if that’s what you’re worried about.”

Puzzled, Dean scratches the back of his head, blankly staring at the book in his hands.

“You know what my parents think about stuff like this,” he explains the disguise lowering his gaze in embarrassment.

Dean sighs with relief, waving goodbye to the prospect of seeing less of Cas from now on. And of failing his exams. But Cas is probably the priority here.

“So you’re gonna keep trying to make a decent human being out of me?”

“Only if you want me to.”

Cas wipes his glasses on the sleeve of his sweater, eyes half closed, soft smile on his lips. That’s when Dean knows that it’s time. It’s their last year of high school and maybe even last year together. And even though it’s enough for him to just be near Cas, sometimes he has to grit his teeth to stop himself from running his hand through his hair, touching his cheek, holding him tighter than he should. He is not ready to lose his best friend because come on, in what world would someone like Cas have feelings for someone like Dean? He’s running out of options here. Either he keeps silently going insane…

Or tries to win his heart.


	2. Chapter 2

During the lunch break, they gather in the school backyard: Sam is sitting beside Dean with Anna and Charlie opposite of them. Dean keeps looking over his shoulder as he waits for Cas who is running late for some reason. Sam rolls his eyes.  


“I’m never gonna fall in love,” he declares.  


Dean looks at him suspiciously.  


“Why is that?”  


“No offence, but I don’t wanna turn into a hopeless softie.”  


“He’s right,” Charlie can’t hold back her smile, “I can’t remember the last time you stopped being your cocky arrogant self around your previous sweethearts.”  


“This must be true love,” Anna plays along, dreamily closing her eyes.  


Dean pretends he is extremely interested in his burger despite suddenly losing his appetite.  


“I’ve no idea what you’re talkin’ about. And aren’t y’all supposed to be on my side?”  


Three pairs of eyes look at him with pity. He drops his head on the table with a moan.  


“Oh, what’s the point. I’ll never have the guts to tell him. What if he never wants to see me again?”  


“Cas is not as prudish as people think,” Anna shrugs. “But Sam would sooner cut his hair than he would get a hint of what’s going on.”  


Sammy proudly blows a strand of hair out of his eyes.  


“Hey, losers!” Ruby, Anna’s classmate, takes the empty sit right next to her. Apart from Sam, she is one year younger than the rest of the company as well. She possessively puts her hand around Anna’s shoulder, blowing a pink bubble with her bubblegum until it pops.  


“Have you guys seen Crowley anywhere?”  


“No,” answers Charlie with a forced but polite smile, discreetly taking Ruby’s hand off her girlfriend’s shoulder. “But knowing him, he’s probably lurking in some dark corner stealing lunch money from little kids.”  


“Wow, someone’s in a bad mood.” Ruby is smirking, totally unimpressed with her hostility. “Anyways, let’s get down to business. Just because I’m such a good girl, I thought I’d let you know about the party Benny is throwing tomorrow night. Crowley promised to get the booze, he’s got a fake ID.”  


She turns her face towards Anna, twirling a lock of hair on her finger.  


“Come. You can also bring your…” she raises an eyebrow glancing over everyone at the table with a doubtful expression, “friends.”  


“We’ll be there,” Anna promises.  


Ruby leaves taking Sam’s untouched sandwich with her, and Anna gives her friends a shy smile as if saying sorry for her behavior.  


“Since when are you interested in parties?” Charlie asks.  


“Since my parents never let me go anywhere.” She kisses her on the cheek, and just like that Charlie is no longer annoyed. “Plus, Dean is inviting Cas.”  


“Dean is doing what?” he is so stunned he almost chokes on his burger.  


“Dim lights, loud music, dancing and alcohol. The perfect recipe for getting together,” Charlie raises her finger admonishingly.  


Dean is still thinking about it when Cas takes the same place that was occupied by Ruby just a minute ago. He is out of breath and there are red spots blooming on his cheeks and neck.  


“Where have you been?” his sister asks. “The lunch is almost over.”  


“Mr. Tran asked me to stay after class. I evidently disrupted the lesson when I started an argument with him about the density of certain chemical elements because well, he was wrong. But while he was telling me how I undermined his authority, we started arguing all over again-”  


“Please, spare us the details,” Charlie pleads, mimicking a snore at the first mention of another dispute with a teacher.  


Dean chuckles, shaking his head and watching his friend hastily devour the peanut butter sandwich. Cas catches his glance.  


“What did I miss?”  


“We’re going to a party,” Sam replies eagerly.  


Dean pats him on the head, bringing him back into the real world, “You ain’t going nowhere, buddy.”  


“That’s not fair,” Sam pouts, but he knows there is no point in protesting.  


“A party?” Cas repeats. “Let’s see. No adults, underage drinking and loud noise after 10 p.m.? Our parents’ worst nightmare. They’ll never let us go.”  


“Are we even related?” Anna snorts. “Michael’s moved to another state just so he wouldn’t have to see Luke, Luke either left home or got kicked out by Dad, and Gabe became a hippie and now lives in a trailer.”  


“Not exactly my life goals,” Cas reasonable notes.  


“My point is that it’s not in our blood to follow orders,” she says, shooting Dean a begging look. Cas looks up at him, too, biting his lip uncertainly. Dean nods in encouragement.  


“They don’t have to know.”

  


Charlie picks Dean up on her beat-up truck, and together they go to the Novaks’ house. It’s already dark outside, and the soft glow of the street lights doesn’t quite reach them, but the four of them make so much noise that it’s a miracle they don’t get caught. Slipping through the backdoor, the siblings climb over the fence, their clothes getting caught on splinters. They jostle their elbows, hushing each other and giggling like five-year-olds before getting in the truck parked in the middle of the street in a hurry. Anna calls shotgun, and Dean finally gets the chance to look over Cas who is sitting with him in the backseat. He can’t stop himself from smiling as he sees the thin blue tie and the tightly buttoned-down white shirt.  


“Cas, wait a minute. You’re gonna wear that? To a party?”  


“This is all I have,” Cas looks down on his clothes in confusion.  


“Okay,” Dean sighs. “That’s not a prom, buddy. Uh, lose the tie.”  


Cas hesitates but obediently unties the knot, handing his tie over to Dean who tosses it to the side.  


“That’s a little better. All right. There we go,” he looks at Cas appraisingly. “And do the buttons – why don't you unbutton it?”  


Cas starts unbuttoning the shirt, and Dean’s throat goes dry. He swallows with an effort and manages to pull himself together just in time.  


“Okay, th-that’s far enough,” he laughs a little and clears his throat, manly patting Cas on the chest. “Yeah, good. All right. Are we there yet?”  


Charlie looks at him in the rearview mirror with an expression on her face that says, “What the hell, Winchester?” She sets her eyes on the road again.  


“Almost there.”  


The moment they step inside, Anna and Charlie get lost in the crowd. Dean tries not to leave Cas alone for too long, knowing how uncomfortable he gets among that many unfamiliar people. But a bit of alcohol changes everything.  


“It’s not the first time you’re doing this though, is it?” Dean points to the plastic cup in his hand, leaning towards his ear to be heard above the music.  


“Dean, I am a Catholic, not a savage,” he lies almost convincingly.  


They find Benny surrounded by a few members of the football team listening to one of his stories with their mouths open. An awkward greeting and a couple of clumsy pats on the back later, Dean retreats to the other corner of the living room. Cas tilts his head, thoughtfully sipping his drink through a straw.  


“Weren’t you a thing for awhile?”  


“Nothing serious,” Dean says as indifferently as possible not knowing where to look. The thought of talking to Cas about his dates and meaningless kisses with someone else makes him flush.  


“Why?”  


Piercing blue eyes are fixed on him. _“Because I was in love with you, you idiot,”_ Dean wants to yell. He shrugs instead.  


It’s somewhere around midnight, and a fair amount of punch later Cas undoes another button showing his collarbones and takes off the glasses putting them in the back pocket. After a heated discussion about demons and witches with Ruby and Meg, he walks over to Dean who’s been listening to his teammate’s rambling about the necessary change of strategy for at least half an hour. Cas holds out his hand, and Dean cocks his eyebrows.  


“I’m inviting you for a dance,” declares he.  


Dean looks around in disbelief making sure it’s not someone’s cruel joke before taking his hand. They join the dancing people, and the air is hot from their body heat. Cas keeps stumbling, having trouble seeing in the semidarkness without his glasses, but Dean doesn’t mind because Cas holds onto his hand to keep his balance.  


“You saved me from the most boring conversation in my life.”  


“You’re welcome,” mumbles Cas, smiling and awkwardly shifting from one foot to another to the beat of the music. “Meg was trying to make me go play Spin-the-Bottle with her, so I had to escape. I suck at dancing.”  


Someone turns the volume up, and they have to lean closer to each other, so close that Dean can see how dilated his pupils are in this dim light, the way his damp dark hair sticks to the forehead, the way his nostrils flare as he breathes heavily.  


“Just relax,” Dean tells him and, barely believing his own nerve, puts his hands on his waist. He guides Cas, feeling the heat of his body through the thin fabric, and his heart is beating so fast he’s afraid everyone can hear it.  


Soon Cas catches the rhythm, moving in unison with him. Dean takes his hands off of him, still feeling the tingling sensation in the tips of his fingers, and for a second he is the happiest person in the whole world.  


The song ends, and the music stops, letting Benny announce that pizza’s been delivered. Taking another cup of punch, Cas collapses onto the sofa and drinks it in one go.  


“Hey, guys, how about some pizza?” Charlie appears with a slice in her hand. “It’s going out like hotcakes.”  


“No, thanks,” Cas shakes his head, looking unhealthily pale.  


“You okay?” Dean asks with concern.  


He nods, but Dean decides to keep an eye on him just in case. He completely forgets about the grand plans he made for that pizza.  


“I think Ruby is flirting with Anna,” Charlie says, lowering her voice. “It’s a pity dueling ain’t in anymore.”  


“Doesn’t she flirt with everyone?” Dean attempts to reassure her. “That doesn’t mean anything. And I’m pretty sure Anna’s not interested in anyone but you.”  


Out of the corner of his eye he can see Meg sitting down next to Cas again, giving him a piece of folded in half paper. Cas unfolds it, reading, hastily crumples it and hides inside his pocket. Clenching his jaw, Dean crosses his arms on the chest and makes himself look away.  


“Anyways, how’s your night going?” Charlie playfully raises an eyebrow, grinning.  


“Not sure.” He is going to say something else, but Cas gets on his feet and comes really close, ignoring his personal space and whispering in his ear, “Dean, I’m not feeling very well.”  


“Okay, that’s enough for today,” Dean comfortingly puts a hand on his shoulder. “Time to go home.”  


Charlie offers to give them a lift, but Cas’ face goes green at the very thought of the road bumps. The night air is quite chilly, but Cas can’t find his trench coat in the pile of other guests’ outerwear, so Dean lends him his leather jacket. They manage to get pretty far from the house when Cas, swaying a little, comes off the road and empties his stomach.  


“I have to tell you something,” he says gloomily. “I’ve never been drunk before.”  


“No shit,” Dean smirks.  


Cas looks so miserable that Dean hugs him around the shoulders. He decides that in the state Cas is currently in he’s bound to wake the whole house, so Dean takes him further up the street to his own residence. If someone is going to get scolded for sneaking away in the middle of the night, he’d rather it was him.  


They manage to get upstairs to Dean’s room without making too much noise. Cas falls onto the bed, not bothering to take off neither the jacket nor the shoes. He cringes as something snaps with a loud crack. He reaches into his back pocket, fishing out the glasses that are now broken in half.  


“Oh no,” he sighs, holding the pieces to his chest. “I’m never gonna see the light again.”  


“Try opening your eyes.”  


He lifts his eyelids to see Dean bending over him with a cup of hot tea in his hands.  


“That’s better,” he props himself up on his elbow, accepting the cup gratefully. “But I still can’t even see your freckles.”  


There is a warm feeling growing in Dean’s chest. He helps Cas with his shoelaces, hiding his face. He wraps sleepily blinking Cas in a blanket and leaves a bottle of water and a couple of aspirins on the bedside table. It’s going to be sunrise soon, and Cas instantly falls asleep. Dean sits on the wide windowsill with his legs, wearily looking through the school notes Cas gave him to stay awake.  


On one hand, he’s glad Cas let himself unwind and relax for awhile. On another hand, alcohol poisoning is not very likely going to help him see Dean in a romantic light, given he remembers anything in the morning. A hot wave on shame runs through his body as he beats himself up for not taking proper care of his friend.  


He’s looking at the doodles of his favorite characters Cas has left on the margins of the page when he dozes off. It takes him a minute to realize who and why is trying to shake him up. Of course, they slept in. Dean feels responsible for what happened last night, so he accompanies Cas back home. They rush each other, completely exhausted by the time they reach the house. Chuck’s car is still in the driveway, and there’s no light in the windows. They exchange relieved smiles and lean against the wall catching their breath.  


“Had fun last night?” Anna looks down on them from the window, making them jump and enjoying the effect.  


“My head is splitting,” Cas shares. “When did you get back?”  


“Just now. Charlie gave me a lift,” she explains. “You guys look like shit.”  


“Thanks,” Dean replies somberly.  


“Cassie, are you waiting for our parents to come and find you?” she tilts her head just like Cas does. “Time to kiss goodbye and go home.”  


Dean goes back lost deep in thoughts about a morning shower, a cup of strong coffee and a few hours of rest. He kicks a small stone he found lying on the road all the way up to his porch, lifting his head only to see John standing in the doorway, arms crossed on his chest. Painfully aware of how early in the morning it is and of the dark circles under his eyes that speak for themselves, Dean steps forward with a heavy heart.


End file.
